3-(2-Furyl)-1-pentanol | 69978-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(2-Furyl)-1-pentanol
• 英文别名: 3-(Furan-2-yl)pentan-1-ol
• CAS: 69978-31-0
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: HAJJJAKLLGYGET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 3-(2-Furyl)-1-pentanol 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 18.0h， 以22.3 mg的产率得到(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid 3-furan-2-yl-pentyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Conjugate Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-2,4,6-Triisopropylphenylsulfonylaldimines with Use of N-Boc-l-Val-Connected Amidophosphane-Copper(I) Catalyst

  摘要：

  Asymmetric conjugate addition of dialkylzinc to alpha,beta-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines 9 was catalyzed by 5 mol % N-BOC-L-valine-connected amidophosphane 5a-Cu-(MeCN)(4)BF4 in the presence of 4 Angstrom MS in toluene to afford, after hydrolysis of an imine to an aldehyde through a short alumina column and reduction with sodium borohydride, the corresponding beta-alkylated alkanols 10 with 67-91% ee in reasonably high yields.

  DOI：

  10.1021/jo0484225
• 作为产物：
  描述：

  diethylzinc 、 (E)-N-[(E)-3-(furan-2-yl)allylidene]-2,4,6-triisopropylbenzenesulfonamide 在 tetrakis(acetonitrile)copper(I)tetrafluoroborate 、 {1(S)-[((2S)-diphenylphosphinomethyl)pyrrolidine-1-carbonyl]-2-methylpropyl}carbamic acid tert-butyl ester aluminum oxide 、 sodium tetrahydroborate 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 6.0h， 生成 3-(2-Furyl)-1-pentanol 、 3-(2-Furyl)-1-pentanol
  参考文献：
  名称：

  Catalytic Asymmetric Conjugate Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-2,4,6-Triisopropylphenylsulfonylaldimines with Use of N-Boc-l-Val-Connected Amidophosphane-Copper(I) Catalyst

  摘要：

  Asymmetric conjugate addition of dialkylzinc to alpha,beta-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines 9 was catalyzed by 5 mol % N-BOC-L-valine-connected amidophosphane 5a-Cu-(MeCN)(4)BF4 in the presence of 4 Angstrom MS in toluene to afford, after hydrolysis of an imine to an aldehyde through a short alumina column and reduction with sodium borohydride, the corresponding beta-alkylated alkanols 10 with 67-91% ee in reasonably high yields.

  DOI：

  10.1021/jo0484225

文献信息

• Fully Biocatalytic Rearrangement of Furans to Spirolactones
  作者：Yu-Chang Liu、J. D. Rolfes、Joel Björklund、Jan Deska

  DOI：10.1021/acscatal.3c00132

  日期：2023.6.2

  building blocks. In a streamlined one-pot reaction cascade, the combination of chloroperoxidase, an oxidase, and an alcohol dehydrogenase renders an efficient reaction cascade for the conversion of hydroxy-functionalized furans to the spirocyclic products. The fully biocatalytic method is successfully employed in the total synthesis of the bioactive natural product (+)-crassalactone D, and as the key

  多酶途径可以制备光学纯的螺内酯结构单元。在简化的一锅反应级联中，氯过氧化物酶、氧化酶和醇脱氢酶的组合提供了一个有效的反应级联，用于将羟基功能化的呋喃转化为螺环产物。该全生物催化方法成功应用于具有生物活性的天然产物(+)-crassalactone D的全合成，并作为产生lanceolactone A的化学酶途径的关键模块。